Vortec swap is doable.
Physically the swap in your case would be pretty simple. Proper bolt pattern intake, that's about all that's required I can think of in terms of what is really different physically, externally, vs. TBI.
However. The problem is the injection system. Vortec makes significantly more power, and the way it does so requires significant changes to timing and fueling. The only ways to get there (keeping it EFI) are to learn PROM tuning, go with Dynamic EFI's EBL, or convert to an aftermarket injection system.
I don't see the Dynamic EFI being a bad option, but a Vortec swap is not a plug and play option unfortunately. All that is, is a stock LO5 swap.
Transmission-wise, the 700R4, in good shape, would be fine behind that motor IMO. Certainly the least amount of effort.